Methyl iodide → N-(3-bromo-5-nitrophenyl)-N-methylacetamide

Participants

Reaction Steps

31.0 g (0.1197 mol) of N-(3-bromo-5-nitrophenyl)-acetamide were dissolved in 240 ml of dimethylformamide and added dropwise within 20 min. to a suspension, cooled at 5° C., of 5.8 g (0.1325 mol) of NaH (60%) in 120 ml of dimethylformamide. Subsequently, the mixture was stirred at room temperature for 1 hr., again cooled to 0-5° C. and 22.30 ml (0.358 mol) of MeI were added thereto. The mixture was stirred at room temperature for 18 hrs., then freed from solvent and the residue was partitioned in water and dichloromethane. The organic phase was washed with sat. sodium chloride solution, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel with ethyl acetate/hexane. There were obtained 29.0 g (88.7%) of N-(3-bromo-5-nitrophenyl)-N-methylacetamide as a brown oil. MS (El): me/e=274,272 (C9H9BrN2O3+).

Provenance & Evidence